2-chloroethylcyclopropyl ether and method of preparing it



Pateflted Mal. 9,

Z-CB'LOROITHYLGYCLOPROPYL ETHER AND METHOD OI PREPARING IT Robert M. Vance, Cleveland, and Amos G. Horney, Worthington, Ohio, assignors to Air Reduction Company Incorporated, New York,

N. Y., a corporation of New York No Drawing. Application June 14, 1944.

Serial No. 540,319

2 Claims. (01. zen-s11) This invention relates to a new chemical compound, 2-chloroethylcyclopropyl ether, and to a method of preparing it.

It is the object of the invention to provide a compound which is useful 'ror various pu ses but primarily as an intermediate in the preparation of other-compounds, for example, the preparation or cyclopropyl vinyl ether, and to afford a method of preparation which is capable of application in relatively large scale commercial operations to produce high yields of the substantially pure compound.

Other objects and advantages of the invention will be apparent as it is better understood by reference to the following specification, in which the preferred embodimentsof the invention are described.

The new compound 2-chloroethylcyclopropyl ether has the structural formula It is a colorless liquid with a characteristic ethereal odor and has a boiling point of 134-434.?

C. at' 748 mm. Other characteristics are ng- 1.013 and 11%- 1.4350

Preparation of the new compound is best effected by cyclization of l-chloro-3-bromo-2-(2- attached to a downward condenser. About 195 grams (3 mols) of zinc dust are added with vigorous-stirring, and the flask is heated until water refluxes in the condenser between the flask and Claisen head. 535 grams (2.3 mols) of the ether are added drop by drop and the temperature is controlled in the reflux condenser so that the product distills over at a moderate rate. The product is separated from the water layer, dried with sodium sulphate and distilled without fractionation-at atmospheric pressure. A yield of 146 grams (1.2 mols) of Z-chloroethylcyclopropyl ether is obtained.

The method as described affords a satisfactory and practicable procedure for the preparation of the desired product which may be carried out with suitable modification of the apparatus used to prepare the product for commercial use.

Various changes may be made in the details of go the procedure without departing from the invention or sacrificing the advantages thereof.

We claim: 1. A new chemical compound, 2-chloroethylcyclopropyl ether with the structural formula:

CH1 l\ cn-o-om-omcx 2. The method of preparing 2-chloroethylcyclochloroethoxy) propane with zinc in water by the reaction cn,arcn-cmci on,

+-Zn water --cm--cmci cn-o-cm-omoi 1-chloro-3-bromo-2-(fichloroethoxy) propane is a new compound having a boiling point of 'ter are placed in a two liter three neck ilask, titted with an addition funnel. stirrer and Ciaisen head chloro-3-bromo-2-(2-chloroethoxy) propane with zinc dust and water.

I ROBERT M. VANCE.

AMOS o. HORNEY. amannoas man The following references are of record in the die of this patent:

UNITED STATES PATENTS Number Name Date 1,941,108 Reppe Dec. 26, 1933 2,024,749 Scott Dec. 7. 1935 2,058,468 Kharasch Oct. 27, 1936 2,148,437 Coleman Feb. 28, 1939 2,299,411 Rust -1 Oct. 20, 1942 2,303,549 Horney Dec. 1, 1942 Kraut: Oct. 5, 1943 

